Top Sarasota Tours, Sightseeing & Cruises - page 2

Discover the calm waterways around Siesta Key, just outside of Sarasota, on this small-group excursion. Choose a kayak or stand up paddleboard, whichever you are more comfortable with, for your journey. Then, follow your guide through the Jim Neville Marine Preserve observing mangrove islands and local wildlife while you paddle towards a secret beach.

Discover the Best of Anna Maria Island with Island Time Boat Tours! Set sail on a private and all-inclusive boat adventure that you’ll remember forever. At Island Time Boat Tours, we provide everything you need for an exciting day on the water, including paddle boards, snorkeling gear, and water floats—all for your convenience! ✨ Meet Your Captains: Our expert captains, Beth and Matt, are not only master licensed but also passionate about showcasing the hidden gems of Anna Maria Island. They'll guide you to the most breathtaking spots! Whether you're looking for a relaxing day or an action-packed adventure, you can feel safe and excited booking your unforgettable experience with Island Time Boat Tours. Why Choose Us? - Customized Itineraries tailored to your interests - Small Group Sizes for a more intimate experience - 5-Star Reviews from happy adventurers—check them out on Google! Book your trip today and get ready for an unforgettable journey

Explore the stunning Sarasota coastline with Tortuga Boat Adventures. Enjoy a private boat tour tailored to your group's needs, whether it's dolphin watching, sunset cruises, or sandbar adventures. With over 15 years of experience, Captain Brian and First Mate Christina ensure a family-friendly atmosphere filled with personalized service and local insights. Take in the natural beauty while spotting playful dolphins and manatees, and enjoy a peaceful day on the water. Perfect for families, romantic getaways, or group outings, these tours create unforgettable memories on the water. - Customizable private boat tours around Sarasota’s coastline - Family-friendly experiences with life jackets for children - Spot dolphins and manatees while enjoying the scenery - Tours range from 3 to 6 hours with convenient pickup options

What sets our 4 Passenger Gas Golf Cart Rentals in Anna Maria apart is the perfect combination of agility, comfort, and customer-first service, featuring the Fastest Delivery Guaranteed if needed! Our 4 seater carts feature a smaller footprint and quick, responsive handling, making them incredibly easy to maneuver through island streets and park in tight beach or restaurant spots—something larger carts simply can’t match. We’ve carefully selected a medium ride height that gives you easy step-in access while still offering ample ground clearance for a smooth, confident ride around the island. Plus, we remove the typical rental stress with free customer pick-up and complimentary gas top-offs if you’re running low and stop by our shop. It’s the ideal blend of convenience, performance, and personalized service—designed to make exploring Anna Maria Island effortless and fun from start to finish. Free parking on our lot when you rent!

Discover the mangroves of Florida with the help of a guide to take you through the waterways of Robinson Preserve on this group kayaking tour. Learn all about the area from your guide and keep your eyes peeled for a chance to spot native birds, fish, and even manatees while you paddle. Your tour guide will also take you up an observation tower to take photos of the scenery.

Explore the serene waters of Clam Bayou on our clear kayak tours, perfect for adventurers of all skill levels. Paddle beneath a stunning canopy of mangroves with a knowledgeable guide and enjoy the possibility of spotting manatees, dolphins, and birds such as herons and egrets in their natural habitat. Take in the scenic beauty just minutes from downtown St. Pete while learning about the local ecosystem. All gear is provided, including transparent kayaks, life jackets, and paddles. The calm waters are ideal for both beginners and experienced paddlers, offering a unique opportunity to see marine life through the transparent kayak hull. Kayak Info: Our clear tandem (2-seat) kayaks have a 385 lb combined weight limit to ensure proper weight distribution and safety. Solo use is available for guests over the limit or for odd-numbered groups—please contact the supplier after booking. Solo riders must not exceed 325 lb for safety and balance.

Join us on Tuesdays January-April for our NEW Venice, FL Tours! Experience a full day of fun on our 10 AM Venice City Sightseeing Tour or our 1 PM Circus Secrets of Venice tour. Discover the history, landmarks, neighborhoods, natural beauty, and things to do in Venice, FL on the Venice City Sightseeing Tour! Offered in partnership with Venice Florida Tours guides. Tours depart from the Venice Area Chamber of Commerce – 597 S Tamiami Trail, Venice, FL 34285. ALL guests must be ages 10+. Every guest must have a paid ticket in order to board. Tour ticket includes FREE Parking!

With Beach Bum Charters you will see the area from a unique perspective as well as get the best guides around!

Splash into an unforgettable adventure where playful dolphins, gentle manatees, and crystal-clear waters await—perfect for first-time snorkelers and nature lovers alike, this private tour is your chance to explore Florida’s marine life up close in a relaxed, shallow-water setting

Discover the delectable highlights of Sarasota's thriving dining scene on this small-group, evening tasting tour. Meet your guide in central Sarasota, and come with an appetite: you'll visit several local restaurants, and will enjoy enough samples to add up to a meal (alcoholic drinks additional expense). As you go, soak up the convivial atmosphere, and learn more about Sarasota's unique culture and culinary offerings.

On this self-guided bicycle tour, you’ll discover how an unlikely cast of characters – from a Fig Newton millionaire, to platform divers who dodged sharks – transformed a barrier island into a beloved community. You’ll encounter the island’s famous “mosquito jail” – a 1927 lockup with barred windows but no glass, where biting insects proved more effective than bars at deterring crime. You’ll pedal past the Roser Memorial Church, built by Charles Roser, who created the Fig Newton cookie and the process to make it then sold his creation Nabisco for a million dollars in 1890 Along the way, you’ll learn about the making of Hollywood’s 1948 film On an Island With You, and explore Bean Point where the island’s first homesteader settled in 1892. You’ll also ride past sites devastated by 2024’s hurricanes and discover how this community of 1,000 residents rallied to rebuild.

With a variety of boat tour options available, visitors can explore the natural beauty of the Gulf, learn about local history, spend the day at a sandbar, witness dolphins and local wildlife, spread loved ones ashes, engagement, wedding, bachelor and bachelorette party. Private charters for a one of a kind personalized experience.

Our Anna Maria Island beach cruiser rentals stand out because they’re built specifically for relaxed, coastal exploring — comfortable upright design, smooth single-speed simplicity, and ready-to-ride setups with baskets, locks, and lights included. The island’s flat, bike-friendly layout makes cruising effortless, whether you’re heading to the beach, Pine Avenue, or a sunset dinner. Unlike crowded parking lots or traffic stress, biking lets you experience the island at a slower, more authentic pace. Free parking on our lot when you rent! It’s not just transportation — it’s part of the Anna Maria lifestyle.

Just west of Sarasota’s city streets, you’ll find the serene shores of Lido Key. Get acquainted with Liquid Blue Outfitters and jump on a unique kayaking tour. You’ll meet at Bird Key Park Preserve where your guide will have a kayak, paddle, and dry bag waiting for you. Explore the marine life around the park, keeping an eye out for marine life swimming nearby.

Increase your chances of spotting manatees and dolphins during an eco-friendly kayak tour of the Lido Key in Sarasota. Ideal for lovers of nature and wildlife, this experience lets you escape the crowds on land and is suitable for both beginner and advanced paddlers. Plus, traveling in a non-motorized vessel means you’re less likely to scare away animals.

Our women’s beach cruiser rentals on Anna Maria Island are designed for effortless island living — featuring upright handlebars, ultra-comfort seats, and smooth, easy handling perfect for beachwear cruising. Each bike is professionally tuned for a safe, reliable ride throughout your stay. With Anna Maria’s compact, bike-friendly layout, you can easily ride to the beach, shops, restaurants, and sunset spots without worrying about parking. It’s the most relaxing, fun, and authentic way to experience the island like a local. Weekly bike rentals include free delivery and pickup if needed. Free parking on our lot when you rent!

Experience an exclusive private dolphin and wildlife tour through the pristine waters of Bradenton Beach and Anna Maria Island! Exploring the waters of Bradenton Beach and Anna Maria Island with a USCG-licensed captain. On this tour, your group will have the entire boat to yourselves as you cruise the stunning Gulf of Mexico coastline and back bays, searching for dolphins, manatees (seasonal), and coastal wildlife in their natural habitat. Your local captain will navigate the grass flats and intracoastal waterways, where dolphins frequently play and feed. During low tide, watch wading birds like herons, egrets, and pelicans on the exposed flats. In season, you may spot manatees grazing in the shallow waters. This personalized eco-tour offers incredible photo opportunities and an intimate connection with Florida's diverse marine life. Book your private adventure today for an unforgettable Anna Maria Island experience!

We are the only paddling outfitter with kayak access to this spectacular area in the clear waters between Anna Maria Island and Longboat Key, which means no crowds and more exclusive wildlife viewing opportunities! Wildlife-viewing here is outstanding! Our expert naturalist guides set the gold standard for hospitality in our beautiful corner of the world and are always very respectful of any wildlife encountered on the tour. While larger groups can easily be accommodated upon request, we always limit our tours to small groups and we are rewarded with a very relaxed and happy group of paddlers. This excursion is perfect for families, couples, groups, and individuals with any level of paddling experience. First-time paddlers are always welcome. If you are looking for an incredibly relaxed and memorable adventure during your visit to Anna Maria Island and Longboat Key, this is it!

It's a private tour for you and your party, up to 6 passengers max. Captain Rachael will be providing a safe, fun, and memorable experience for you to hold onto. Her local knowledge adds to the experience by finding dolphins and telling you about the local area. She also has a bathroom onboard and a bow bimini shade if you prefer to stay out of the sun.

Combine a trolley ride with drinks and live entertainment on this interactive murder mystery trolley experience in Sarasota. Audience participation encouraged: get into the spirit by donning a circus costume and reading lines from a script, and see if you can help solve the mystery of who killed the circus queen. Includes alcoholic beverages.

Discover the charming allure of St. Armands Circle, once owned by circus magnate John Ringling, on this engaging afternoon tour. Delight in a unique blend of shopping and tasting experiences as you browse stylish boutiques while sampling gourmet tea and olive oil. Enjoy a Mediterranean-inspired sampler plate paired with a glass of bubbles, and explore a luxury art and gift boutique with another glass in hand. Conclude your day with a personal shopping experience or visit the enchanting St. Armands Magical Garden, topped off with a sweet treat to savor the day. - Explore locally-owned shops and boutiques on historic St. Armands Circle - Enjoy a Mediterranean-inspired tasting platter and bubbly - Participate in tea and olive oil sampling for a culinary experience - End with a visit to the St. Armands Magical Garden or personal shopping time

*If more than one Scoot Coupe is needed, please make a separate rental purchase for each additional Scoot Coupe. The Scoot Coupe is the ultimate side-by-side scooter, built for two passengers to ride together in comfort and style on Anna Maria Island. One person drives while the other relaxes, takes photos, and soaks in the coastal views — no awkward back seat, just easy conversation and shared memories. Cruise past island landmarks, beach access points, shops, and waterfront restaurants with effortless parking along the way. Get ready for sunshine, sea breezes, and the most fun you can have exploring Anna Maria together. Free parking on our lot when you rent!

For something different than beaches, discover one of Sarasota's most unique communities on an insider’s tour of Pinecraft, an Amish vacation enclave right on the outskirts of town. Led by a guide with personal connections to the local Amish and Mennonite communities, learn about their roots in Florida, traditional customs, and beliefs. You’ll also have the chance to shop for handmade gifts and sample famous pie at an Amish cafe.

Let your local guide, who’s also an actor and songwriter, show you around Sarasota on this cabaret-style tour of the city. Start with free wine or beer in the Trolley Cottage Tiki Bar before setting off in an air-conditioned trolley, with stops at Lido Beach in time for sunset, and Sun King Brewery for some craft beer tasting and a tour.